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Merck

T3383

Tetracycline hydrochloride

≥95% (European Pharmacopoeia HPLC assay)

Synonym(s):

4-Epitetracycline hydrochloride, Achromycin hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C22H24N2O8 · HCl
CAS Number:
64-75-5
Molecular Weight:
480.90
UNSPSC Code:
51284043
NACRES:
NA.76
PubChem Substance ID:
24900135
EC Number:
200-593-8
Beilstein/REAXYS Number:
3844873
MDL number:
MFCD00078142

Product Name

Tetracycline hydrochloride, ≥95% (European Pharmacopoeia HPLC assay)

InChI key

XMEVHPAGJVLHIG-FMZCEJRJSA-N

InChI

1S/C22H24N2O8.ClH/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28;/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30);1H/t9-,10-,15-,21+,22-;/m0./s1

SMILES string

Cl.CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c4c(O)cccc4[C@@]3(C)O

assay

≥95% (European Pharmacopoeia HPLC assay)

form

powder

storage condition

(Keep container tightly closed in a dry and well-ventilated place.)

color

yellow

mp

220-223 °C (lit.)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

protein synthesis | interferes

storage temp.

−20°C

Quality Level

200

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Application

Tetracycline is a broad spectrum polyketide antibiotic with clinical uses in treating bacterial infections such as Rocky Mountain spotted fever, typush fever, tick fevers, Q fever, and Brill-Zinsser disease and to treat upper respiratory infections and acne. It has been used in studies of multidrug resistance and potential side effects including acute pancreatitis. It is recommended for use in cell culture applications at 10 mg/L.

Biochem/physiol Actions

Mode of Action: Tetracycline passively diffuses through proin channels in the cell membrane, binding to 30S ribosomes and inhibits protein synthesis by preventing access of aminoacyl tRNA to the acceptor site on the mRNA-ribosome complex. It also binds to the bacterial 50S ribosomal subunit, altering the membrane and causing intracellular components to leak from bacterial cells. The inhibitory effects can be reversed by washing, suggesting that it is the reversibly bound antibiotic, and not the irreversibly bound drug, that is responsible for antibacterial action.

Mode of Resistance: The effects are inactivated via a loss of cell wall permeability.

Antimicrobial spectrum: Includes a wide range of antimicrobial activity against gram-positive and gram-negative bacteria.

Disclaimer

This product should be frozen below 0°C and protected from light and moisture. In these conditions, the product has been shown to retain activity for 4 years. Stock solutions should be stored at -20°C and are stable at 37°C for 4 days.

General description

Chemical structure: tetracycline

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Preparation Note

The product is freely soluble in water, soluble in methanol and ethanol but is insoluble in ether and hydrocarbons. In water, the product yields a clear, yellow-orange solution with heating and in 95% ethanol, 50 mg dissolved in 4 mL with heating yields a clear, yellow-green solution. Tetracycline is rapidly destroyed by alkali hydroxide solutions and standing water solutions become turbid due to hydrolysis and precipitation. The potency of tetracycline is reduced in solutions with pH below 2.

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Warning

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000436215
0000436215
0000436216
0000436216
0000373512

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Abulaziz Juma et al.
Frontiers in microbiology, 11, 1477-1477 (2020-08-01)
One current strategy to deal with the serious issue of antibiotic resistance is to use biosurfactants, weak antimicrobials in their own right, with antibiotics in order to extend the efficacy of antibiotics. Although an adjuvant effect has been observed, the
Yuping Cao et al.
mSystems, 6(6), e0098821-e0098821 (2021-11-03)
Assembly of a resistome in parallel with the establishment of a microbial community is not well understood. Germfree models can reveal microbiota interactions and shed light on bacterial colonization and resistance development under antibiotic pressure. In this study, we exposed
Rachid Elaini et al.
Insects, 11(10) (2020-10-01)
The Mediterranean fruit fly (medfly), Ceratitis capitata, is a significant pest of stone and pome fruit that causes considerable economic losses worldwide. Current control is primarily based on insecticides, which are often mixed with protein baits. Oxitec has developed a
Diego López-Márquez et al.
Plant methods, 16, 41-41 (2020-03-25)
Small RNAs are sequence-dependent negative regulators of gene expression involved in many relevant plant processes such as development, genome stability, or stress response. Functional characterization of sRNAs in plants typically relies on the modification of the steady state levels of
Huanhuan Jia et al.
Frontiers in cell and developmental biology, 8, 83-83 (2020-03-07)
To determine the relationship between maternal bone resorption and bone development in fetuses. Female SD rats were injected with either fluorescent calcium indicator calcein alone or together with tetracycline 1 week before pregnancy, followed by fluorescence detection in fetal tibias
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